Pharmaceutical products.



subcutaneous injection.

j UNITED STATES PATENT OFFICE. MAX ENGELMANN, or ELBERF'ELD;eninvranrjlissrenon mumummma vonm. FRIED'B. BAYER & C0501 ELBZERFELD, GERMANY, A 'CQIWOBATIQN OF GERMANY.

PHARMACEUTICAL rnonucrs.

1,034,092. No Drawing.

Application filed October 6, 1910. Serial mrszatgmv.

Specification of Letters Batent; 'Piliifllliifid Jilly 30, 1912.

salicylicum) which are prepared from the 1 known ortho-oxy-mercuric salicy1ic acid anhydrid (hydrargyrum salicylicum of the German: Pharmacopm'a) by treating it with alkali and an imino compound containing in addition to the imino radical a group imparting an acid character to the. compoun or with the alkali salts .of suchan imino compound. I have now found that in this process other oxymercuric carboxylic acid compounds, especially oXymercur-ic carboxylic acids and their anhydrids'can be used instead of the salicylate of mercuric oxid e.. g.

the oxymercuric benzoic acid anhydrid (see B-em'ohte der Deutschen Ohemischevi Gesellschaft'35 p."2870). The new compounds thus obtained which contain in their molecule the characteristic group K I in which Me means metal and R an aromatic nucleus, are whitish odorless com pounds which are 'very easily soluble inwater and insoluble in ether. They have proved to be valuable 'anti'syphilitica char-' acterized by a mild action and as they are not irritating and not corrosive they are highly valuable for internal application. especially for subcutaneous injection. They contain the mercury so firmly combined that on adding a diluted solution of caustic alkali or a cold solution of ammonium sulfid'no precipitate is obtained. A solution of from 0.1-0.2 grams'may be used for one In order to illustrate the new process more fully the following examples; are given, the parts being by weight: 170-parts of the oxymerouric meta-oXy-benzoic acid anhydrid (obtainable by heating mercuric oxid with meta-oxy-benzoic acid) are added" to a solution of '100 parts of the sodiunrsalt of diethylbarbituric acid in 1000 parts of water. i The resulting solutionisfiltered' and the filtrate" is evaporated in coma.

whitish or stalline compound separates in crystals; t is easily soluble in water with a neutral reaction; insoluble inalcohol, ether,

lbenzene, acetone and chloroform and is probably produced following equation} accordance with the 360 'partsof the oxymercuridorthorchlor benzolc acid anhydrid havingfmost probably the formula: v K i are mixed with 1000 parts of normal NaOH and,113 parts of the imid of glutaric acid are added. After one hour the solution is filtered and the filtrate is evapOrated- The new compound separates in crystals, The whitish product is easily soluble in water, insoluble in alcohol, ether and benzenciand is probably'produced 1n accordance withthe following equation:

v Qtheirimino compounds, suchas succinicj imld, Inono-ethyl-barbituric acid, dipro'pylbarbituric' acid, etc.',;maybe used or other 'll [I ,the mercuric salt' of-the sulfoanthranilic a valuable therapeutics,

acid 'anhydrid, which canbe obtained by treating -acetyl-sulfo-anthranilic acid with HgO and glacial acetic acid, or of nitro benzoic acid anhydrid, etc.

1. The new mercury compounds containing in their molecule the. characteristic group:

in which Me stands for metal, and R for an aromatic radical unsubstituted by hydroXyl in ortho-position to the CO group which compounds are whitish powders easily soluble in water and insoluble in ether, and containing the mercury so firmly combined that the aqueous solutions do not give any precipitate on the addition of dilute caustic soda lye or a cold solution of ammonium sulfid; and being valuable therapeutics, substantially as described.

2. The new mercury compounds containing in their molecule the characteristic group in which Me stands for metal, and R for an aromatic nucleus substituted in meta-post tion to the CO group, which compounds are whitish powders, easily soluble in water and insoluble in ether, and containing the mercury so firmly combined that the aqueous solutions do not give any precipitate on the addition of dilute caustic soda lye or a cold solution of ammonium sulfid; and being substantially as described. 3. The new mercury compounds containing in their molecule the characteristic gr 0111) i R COOMe in which Me stands for metal, and R for an aromatic nucleus substituted by OH in meta position to the 00 group, which compounds are whitish powders, easily soluble in water and insoluble in ether, and contaming the mercury so firmly combinedthatthe aqueous solutions do not give any precipltate on the addition of dilute caustic soda lye or a cold solution of ammonium sulfid; and being valuable therapeutics, substantially as described.

. 4. The'new mercury compounds contain' mg 1n their molecule the characteristic group in which Me stands for metal, which compounds are whitish powders, easily soluble in water and insoluble in ether, and containing the mercury so firmly combined that the aqueous solutionsido not give any precipitate on the addition'of dilute caustic soda lye or a cold solution of ammonium sulfid; and being valuable therapeutics, substantially as, described.

5. The new mercury compounds containing in their molecule the characteristic group COOMe c in which Me stands for metal, X for the radical of a barbituric acid, and R for an aromatic nucleus substituted in meta-position to the CO group, which compounds are whitish powders, easily soluble in water and insoluble in ether, and containing the I mercury so firmly combined that the aqueous solutions do not give any precipitate on the addition of dilute caustlc soda lye or a. cold solution of ammonium sulfid; and being valuable therapeutics, substantiallyas described.

6. The new mercury compounds containing in their molecule the characteristic group in which Me stands for metal, X for the radical of a barbituric acid and R for an aromatic nucleus substituted by OH in meta-position to the CO group, which compounds are whitish powders, easily soluble in water and insoluble in ether, and containing the mercury so firmly combined that the aqueous solutions do not give any precipitate on the addition of dllute caustic soda lye or a cold solution of ammonium sulfid; and being valuable therapeutics, substantially as described.

7. The new mercury compounds containing in their molecule the characteristic group most probably the following molecular formula:

on i -COONa being a whitish powder, easily soluble in Water but insoluble in ether, and containing the mercury so firmly bound that its aqueous solution does not give any precipitate on the addition of dilute caustic soda lye or a cold solution of ammonium sulfid; and being a Valuable therapeutic, substantially as described. .A

In testimony whereof I have hereunto set my hand in the presence of two subscribing Witnesses.

MAX ENGELMANN. [1 s.] 

